NP-MRD: Showing NP-Card for (1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one (NP0160102)

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Record Information

Version

2.0

Created at

2022-09-02 17:59:07 UTC

Updated at

2022-09-02 17:59:07 UTC

NP-MRD ID

NP0160102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one

Description

(1S,4aS,5R,6S,8aR)-5-[(2H-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-decahydronaphthalen-2-one belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. (1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one is found in Ferula assa-foetida. Based on a literature review very few articles have been published on (1S,4aS,5R,6S,8aR)-5-[(2H-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-decahydronaphthalen-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022219592D          

 27 30  0  0  1  0            999 V2000
   -2.9078   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1196   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8942    0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4570    1.4857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2815    1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198    2.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4071    2.9137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1953    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452    0.7284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1164    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
M  END


  Mrv1652309022219592D          

 27 30  0  0  1  0            999 V2000
   -2.9078   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1196   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8942    0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4570    1.4857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2815    1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198    2.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4071    2.9137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1953    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452    0.7284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1164    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@]2(C)[C@H](C)C(=O)CC[C@@H]2[C@]1(C)COC1=CC=C2C=CCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O3/c1-16-11-12-23(3)17(2)20(25)9-10-22(23)24(16,4)15-27-19-8-7-18-6-5-13-26-21(18)14-19/h5-8,14,16-17,22H,9-13,15H2,1-4H3/t16-,17+,22-,23-,24+/m0/s1

> <INCHI_KEY>
UXUTZFNIXIHZJK-SBWRPUSSSA-N

> <FORMULA>
C24H32O3

> <MOLECULAR_WEIGHT>
368.517

> <EXACT_MASS>
368.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.488336648362775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,5R,6S,8aR)-5-[(2H-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-decahydronaphthalen-2-one

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
5.461614767

> <ALOGPS_LOGS>
-6.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.566979519128078

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
108.73729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.45e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,5R,6S,8aR)-5-[(2H-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1H-naphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.428  -2.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.151  -1.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.690  -1.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.413   0.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.597   1.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.136   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.320   2.773   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.859   2.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.504   4.079   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.227   5.439   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.965   4.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.242   2.666   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.058   1.360   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.951   0.675   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14                                                  
CONECT   14   13    2   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₃

Average Mass

368.5170 Da

Monoisotopic Mass

368.23514 Da

IUPAC Name

(1S,4aS,5R,6S,8aR)-5-[(2H-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-decahydronaphthalen-2-one

Traditional Name

(1S,4aS,5R,6S,8aR)-5-[(2H-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1H-naphthalen-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@]2(C)[C@H](C)C(=O)CC[C@@H]2[C@]1(C)COC1=CC=C2C=CCOC2=C1

InChI Identifier

InChI=1S/C24H32O3/c1-16-11-12-23(3)17(2)20(25)9-10-22(23)24(16,4)15-27-19-8-7-18-6-5-13-26-21(18)14-19/h5-8,14,16-17,22H,9-13,15H2,1-4H3/t16-,17+,22-,23-,24+/m0/s1

InChI Key

UXUTZFNIXIHZJK-SBWRPUSSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ferula assa-foetida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Alkyl aryl ether
Benzenoid
Cyclic ketone
Ketone
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.6	ALOGPS
logP	5.46	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.74 m³·mol⁻¹	ChemAxon
Polarizability	42.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162944975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one (NP0160102)

MOL for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

3D MOL for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

3D SDF for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

3D-SDF for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

PDB for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

3D PDB for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

SMILES for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

INCHI for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

Structure for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)

3D Structure for NP0160102 ((1s,4as,5r,6s,8ar)-5-[(2h-chromen-7-yloxy)methyl]-1,5,6,8a-tetramethyl-hexahydro-1h-naphthalen-2-one)